I think there are two kinds of entrepreneurs, and sometimes, you can be both. There is the kind that starts businesses, and there is the kind that builds businesses.

The kind of entrepreneur who starts businesses but usually doesn’t like running or building them are typically serial entrepreneurs. How can you spot one? They:

Have an idea a minute and a bit of ADD – they are attracted to bright shiny objects – they can’t focus

Would rather generate 1 good and idea and 19 bad ones than just 1 good one

Are always thinking about the next thing, only excited by the possibility of what could be, not by what is

Are more philosophical and theoretical than practical

Probably shouldn’t run businesses for more than a few months

Are likely to frustrate everyone around them and get bored themselves

Are really fun at cocktail parties

Say things like “I thought of auctions online way before eBay!”

The second kind of entrepreneur is the kind of person who can run businesses but may or may not come up with the idea. Typically, these people:

Care about success, not about having the idea

Love to make things work

Would rather generate 1 idea and execute it well than 2 ideas

Are problem solvers

Are great with people

May be less fun at cocktail parties, but you’d want them on your team in a game of paintball or laser tag

It’s the rare one who can do both of these things well. But you know them when you see them. Think Dell or Microsoft…or even Apple in a roundabout way if you consider the fact that Jobs hired Cook (and others) to partner with them to run the business.

Fatal System Error: The Hunt for the New Crime Lords Who Are Bringing Down the Internet, by Joseph Menn (book, kindle) was a bit of a disappointment. I was really hoping for more of an explanation of how the “business” of Internet crime works — what the economics are like, what the landscape/scope/sectors are like, who the players are.

What I got was a bit of a true crime novel, the story of Barrett Lyon and Andy Crocker, who are respectively a geek and a cop, and their very specific stories of tracking down a handful of internet criminals around a handful of technical tactics (DDOS attacks and botnets). It wasn’t bad, the stories were ok and occasionally entertaining, but it was very narrow.

It felt to me like there is a much more interesting story to tell around criminals who USE the Internet to commit crimes as opposed to people attacking the infrastructure. Has anyone ever run across a book like that?

You Can’t Teach a Cat How to Bark, But You Might be Able to Teach it How to Walk on its Hind Legs

My co-founder George and I have had this saying for a while. Cats don’t bark. They can’t. Never will. They also don’t usually walk on their hind legs in the wild, but some of them, after some training, could probably be taught to do so.

Working with people on career evolution sometimes follows that same path. Lots of the time, an employee’s career evolution is natural and goes well. They’re playing to their strengths, in their sweet spot, progressing along nicely. But often that’s not the case. And it goes both ways. Some employees want something different. The sales rep wants to be a sales manager. The product manager wants to try marketing. Sometimes the organization needs something different out of the person. Be a stronger manager. Be more collaborative. Acquire more domain or functional expertise.

These transitions might or might not be difficult. It completely depends on the person involved and the competencies required for the new role. And that’s where the barking cat comes into play. There’s more art than science here, but as a manager or as the employee, figuring out the gap between existing strengths/experience and the required competencies for the new job, and whether the missing elements *can* be taught or not is the exercise at hand.

I’m not sure there’s a useful rule of thumb here, either. I had a boss once many years ago who said you can teach smart people how to do anything other than sales. Another boss said you can teach anyone any fact, but you can’t teach anyone empathy. Both of these feel too one-size-fits-all for me. One thing we do at Return Path from time to time is encourage an employee facing some kind of stretch transition (for whatever reason) to participate in or run a short-term side project with a mentor that lets them flex some relevant new muscles. Essentially we let them try it on for size.

OnlyOnce is 8 years old this week, which is hard to believe. So it is fitting that I got halfway through a new post this morning, then a little alarm bell went off in my head that I had written something similar before. The topic is around moderation versus extremes. I first wrote about this topic in 2005 in a post called Shifting Gears but I have thought about it more recently in a different way.

Instead of phrasing this as a struggle between “Meden Agan,” which is Greek for “everything in moderation,” and “Gor oder gornischt,” which is Yiddish for “all or nothing,” I’d like to focus here on the value of occasionally going to an extreme. And that value is around learning. Let me give three examples:

-We were having a buy vs. build conversation at work a few months back as we were considering an acquisition. Some people in the room had an emotional bias towards buy; others toward build. So we framed the debate this way: “Would you acquire the company for $1 instead of building the technology?” (Yes!) “Would you buy it for $10mm?” (No!) Taking the conversation to the extremes allowed us to focus on a rational answer as opposed to an emotional one — where is the price where buy and build are in equilibrium?

– With my colleague Andrea, I completed a 5-day juice fast a few weeks back. It was good and interesting on a bunch of levels. But I came away with two really interesting learnings that I only got from being extreme for a few days: I like fruits and veggies (and veggie juices) a lot and don’t consume enough of them; and I sleep MUCH better at night on a relatively empty stomach

– Last year, I overhauled my “operating system” at work to stop interviewing all candidates for all jobs and stop doing 90-day 1:1 meetings with all new employees as well. I wrote about this in Retail, No Longer. What finally convinced me to do it was something one of my colleagues said to me, which was “Will you be able to keep these activities up when we have 500 employees?” (No) “So what is the difference if you stop now and save time vs. stopping in 6 months?” Thinking about the extreme got me to realize the full spectrum

It may not be great to live at the extremes, but I find extremes to be great places to learn and develop a good sense of what normal or moderate or real is.

I was talking to a CEO the other day who believed it was “wrong” (literally, his word) to meet directly 1:1 with people in the organization who did not report to him. I’ve heard from other CEOs in the past that they’re casual or informal or sporadic about this practice, but I’ve never heard someone articulate before that they actively stayed away from it. The CEO in question’s feeling was that these meetings, which I call Skip-Level Meetings, disempowers managers.

I couldn’t disagree more. I have found Skip-Level Meetings to be an indispensable part of my management and leadership routine and have done them for years. If your culture is set up such that you as CEO can’t interact directly and regularly with people in your organization other than the 5-8 people who report to you, you are missing out on great opportunities to learn from and have an impact on those around you.

That said, there is an art to doing these meetings right, in ways that don’t disempower people or encourage chaos. Some of these themes will echo other things I’ve written in recent posts like Moments of Truth and Scaling Me. My five rules for doing Skip-Level Meetings are:

Make them predictable. Have them on a regular schedule, whatever that is. The schedule doesn’t have to be uniform across all these meetings. I have some Skip-Levels that I do monthly, some quarterly, some once a year, some “whenever I am in town.”

Use a consistent format. I always have a few questions I ask people in these meetings – things about their key initiatives, their people, their roadblocks, what I can do to help, what their POV is about the company direction and performance, how they are feeling about their role and growth. I also expect that people will come with questions or topics for me. If I have more meaty ad hoc topics, I’ll let the person know ahead of time.

Vary the location. When I have regular Skip-Levels with a given person, I try to do the occasional one over a meal or drink to make it a little more social. For remote check-ins, I now always do Skype or Videophone.

Do groups. Sometimes group skip-levels are fun and really enlightening, either with a full team, or with a cross-section of skip-levels from other teams. Watching people relate to each other gives you a really different view into team dynamics.

Close the loop. I almost always check-in with the person’s manager BEFORE AND AFTER a Skip-Level. Before, I ask what the issues are, if there is anything I should push on or ask. After, I report back on the meeting, especially if there are things the person and I discussed that are out of scope for the person’s job or goals, so there are no surprises.

I’m sure there are other things I do as well, but I can’t imagine running the company without this practice. Doing it often and well EMPOWERS people in the company…I’d argue that managers who feel disempowered by it aren’t managers you necessarily want in your business unless you really run a command-and-control shop.